The present invention relates to the use of 2-(N-phenylamino)pyrimidines of the formula I, 
where:
R1, R3 independently of one another are cyano, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals alkyl, alkenyl and alkynyl may be substituted by cyano, halogen, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, or are C3-C8-cycloalkyl or a group C(xe2x95x90NORx)Ry;
Rx is hydrogen, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals alkyl, alkenyl and alkynyl may be substituted by cyano, halogen, C1-C4-alkoxy or phenyl;
Ry is hydrogen, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals alkyl, alkenyl and alkynyl may be substituted by cyano, halogen or C1-C4-alkoxy;
R2 is halogen, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals alkyl, alkenyl and alkynyl may be substituted by cyano, halogen, C1-C4-alkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together with the two linking carbon atoms form a fused-on partially unsaturated 4- to 8-membered ring which may be up to trisubstituted by identical or different substituents selected from the group consisting of C1-C4-alkyl, halogen and C1-C4-alkoxycarbonyl, which may contain a carbonyl group and/or, in addition to the multiple bond of the pyrimidine ring, a double bond and/or which may be interrupted by O, S or Nxe2x80x94(C1-C4-alkyl);
R4 to R8 independently of one another are hydrogen, cyano, halogen, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
Ra, Rb are C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, each of which may be substituted by cyano, halogen, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl, or are phenyl which may carry one to three substituents selected from the group consisting of halogen and C1-C4-alkyl;
m is 0, 1 or 2;
as fungicides.
Fungicidal 2-(N-phenylamino)pyrimidines carrying a hydrogen atom in the 5-position of the pyrimidine ring are known from EP-A 224 339, EP-A 270 111, EP-A 310 550, EP-A 457 726, DD 151404 and JP 03/271278.
2-(N-phenylamino)pyrimidines substituted in the 5-position have been described as intermediates for herbicidally active compounds (EP-A 337 944) and as pharmaceutics (WO-A 97/19065).
Finally, fungicidal 2-(N-phenylamino)pyrimidines which may be substituted in the 5-position and which carry a specific 2-nitrophenyl radical at the amino function are known from EP-A 172 786.
However, the compounds mentioned in EP-A 172 786 do not always fully meet the requirements which have to be met by active compounds in practice.
It is an object of the present invention to provide fungicidally active compounds having improved properties.
We have found that this object is achieved by the abovementioned compounds, some of which have already been mentioned in the publications EP-A 337 944 and WO-A 97/19065, which are outstandingly suitable for controlling harmful fungi. In addition, we have found novel 2-(N-phenylamino)pyrimidines having improved fungicidal activity.
It is a common feature of all aminopyrimidines according to the invention, both the novel aminopyrimidines and those known from EP-A 337 944 and WO-A 97/19065, that they carry hydrophobic substituents in each of positions 4, 5 and 6.
The novel 2-(N-phenylamino)pyrimidines can be prepared similarly to methods known from the literature. Particularly suitable are the process routes shown in Schemes 1 and 2. 
The condensation reaction of the guanidines II with 1,3-dicarbonyl compounds of the formula III to give the 2-(N-phenylamino)pyrimidines I can be carried out as described in EP-A 337 944 and the literature cited therein.
With regard to the synthesis of the guanidines II, reference is made to Houben-Weyl, Methoden der Organischen Chemie, Stuttgart, Vol. VIII pp. 98, 180 to 189. The 1,3-diketones III can be prepared, for example, either by a) Claisen condensation or by b) alkylation or halogenation of a 1,3-diketone which is unsubstituted in the 2-position (Organikum, 1993 Barth Verlagsgesellschaft Leipzig, a) p.487 b) p. 536). 
The preparation of the 2-(N-phenylamino)pyrimidines I starting from aniline derivatives of the formula IV and pyrimidine derivatives of the formula V where X is a nucleophilically replaceable group, such as halogen or C1-C4-alkylsulfonyl, is described in EP-A 337 944.
The compounds I according to the invention in which R3 is C(xe2x95x90NORx)Ry are preferably prepared from the aldehydes VI (see Scheme 3), and the aldehydes VI for their part can be synthesized similarly to EP-A 457 726.
Compounds Ia in which R3 is CH(xe2x95x90NORx) are obtained by reacting the aldehydes VI with the alkoxyamines VII under conditions known per se (Scheme 3).
Moreover, the aldehydes VI can be converted under conditions known per se with organometallic reagents, such as Grignard reagents VIII (Ryxe2x80x94Mgxe2x80x94X; Xxe2x95x90Cl, Br, I), into the secondary alcohols IX.
The oxidation of these alcohols IX, preferably according to Swern using oxalyl chloride/DMSO, gives the ketones X which for their part can be reacted with alkoxyamines VII to give the compounds Ib according to the invention. 
The active compounds Ic in which R3 is cyano (Scheme 4) can preferably be prepared by reacting the aldehydes VI with hydroxylamine, followed by dehydration of the resulting oximes XI (similarly to EP-A 457 726). 
In the definition of the compounds I given at the outset, collective terms which represent individual enumerations of each of the group members were used for the radicals R1 to R8, Rx and Ry and Ra and Rb. The radicals alkyl, alkoxy, alkoxycarbonyl, alkenyl and alkynyl can be straight-chain or branched.
Examples of meanings are:
halogen: fluorine, chlorine, bromine or iodine;
C1-C4-alkyl: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
C1-C8-alkyl: C1-C4-alkyl, as mentioned above, and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-3-methylpropyl, heptyl, octyl or 2-ethylhexyl;
C1-C2-haloalkyl: a C1-C2-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;
C1-C4-alkoxy and the alkoxy moieties of C1-C4-alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
C1-C2-haloalkoxy: a C1-C2-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy;
C2-C6-alkenyl: ethylene, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
C2-C6-alkynyl: ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1-ethyl-1-methyl-2-propynyl;
C3-C8-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
With a view to their use as fungicides, preference is given to 2-(N-phenylamino)pyrimidines I which have the following substituents, the preference existing in each case alone or in combination:
R1, R3 are cyano, C1-C8-alkyl, propynyl, C1-C2-haloalkyl, cyclopropyl or a group C(xe2x95x90NORx)Ry;
R2 is halogen or C1-C8-alkyl;
R4 to R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb);
Ra, Rb are C1-C4-alkyl.
Particular preference is given to 2-(N-phenylamino)pyrimidines I having the following substituents, the preference existing in each case alone or in combination:
R1, R3 are cyano, methyl, ethyl, cyclopropyl, CH(xe2x95x90NOCH3), CH(xe2x95x90NOC2H5), C(xe2x95x90NOCH3)CH3 or C(xe2x95x90NOC2H5)CH3;
R2 is fluorine, chlorine, methyl or ethyl;
R4 to R8 independently of one another are hydrogen, cyano, halogen or C1-C4-alkyl.
Most preference is given to 2-(N-phenylamino)pyrimidines I having the following substituents, the preference existing in each case alone or in combination.
R1 is methyl or cyclopropyl;
R2 is methyl or fluorine;
R3 is CH(xe2x95x90NOCH3), CH(xe2x95x90NOC2H5), C(xe2x95x90NOCH3)CH3, C(xe2x95x90NOC2H5)CH3, cyano or methyl and
R4 to R8 are hydrogen.
The following groups of active compounds are preferred owing to their pronounced plant-fungicidal activity.
Group Ia: 2-(N-phenylamino)pyrimidines of the formula I in which
R1, R3 are cyano, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C8-cycloalkyl;
R2 is halogen, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C2-haloalkyl;
R4, R6, R8 independently of one another are hydrogen, cyano, halogen, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
R5, R7 independently of one another are hydrogen, cyano, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
Ra, Rb are C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, each of which may be substituted by cyano, halogen, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl, or are phenyl which may carry one to three substituents selected from the group consisting of halogen and C1-C4-alkyl, and
m is 0, 1 or 2.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Ia in which
R1 is cyano, methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R2 is methyl, ethyl, fluorine or chlorine;
R3 is methyl;
R4, R6, R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl;
R5, R7 independently of one another are hydrogen, cyano, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl and
Ra, Rb are C1-C4-alkyl.
Group Ib: 2-(N-phenylamino)pyrimidines of the formula I in which
R1 is cyano or C2-C6-alkynyl and the radicals R2 to R8 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Ib in which
R1 is cyano or propynyl;
R2 is halogen or C1-C8-alkyl and is preferably fluorine, chlorine, methyl or ethyl;
R3 is cyano, C1-C8-alkyl, propynyl, C1-C2-haloalkyl or cyclopropyl and is preferably methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R4 to R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl and
Ra, Rb are C1-C4-alkyl.
Group Ic: 2-(N-phenylamino)pyrimidines of the formula I in which
R4 to R8 are hydrogen and the radicals R1 to R3 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Ic in which
R1, R3 are cyano, C1-CB-alkyl, propynyl, C1-C2-haloalkyl or cyclopropyl and are preferably methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R2 is halogen or C1-C8-alkyl and is preferably fluorine, chlorine, methyl or ethyl and
R4 to R8 are hydrogen.
Group Id: 2-(N-phenylamino)pyrimidines of the formula I in which
R2 is halogen;
R4 , R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkoxy, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
R5 to R7 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
Ra, Rb are C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, each of which may be substituted by cyano, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl, or are phenyl, which may carry one to three substituents selected from the group consisting of halogen and C1-C4-alkyl, and
the radicals R1 and R3 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Id in which
R1, R3 are cyano, C1-C8-alkyl, propynyl, C1-C2-haloalkyl or cyclopropyl and are preferably methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R2 is fluorine or chlorine;
R4, R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl;
R5 to R7 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl and
Ra, Rb are C1-C4-alkyl.
Group Ie: 2-(N-phenylamino)pyrimidines of the formula I in which
R1, R3 are C1-C8-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the radicals alkenyl and alkynyl may be substituted by cyano, halogen, C1-C4-alkoxy or C1-C4-alkoxycarbonyl;
R2 is C1-C8-alkyl, C2-C6-alkenyl or C2-C6-alkynyl;
R5, R7 independently of one another are hydrogen, cyano, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
the radicals R4, R6 and R8 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Ie in which
R1, R3 are methyl, ethyl, n-propyl or propynyl;
R2 is methyl, ethyl or n-propyl;
R4, R6, R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl;
R5, R7 independently of one another are hydrogen, cyano, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, cyano, C1-C4-alkyl or C1-C2-haloalkyl and
Ra, Rb are C1-C4-alkyl.
Group If: 2-(N-phenylamino)pyrimidines of the formula I in which
R4, R8 are hydrogen;
R5, R7 independently of one another are hydrogen, cyano, C1-C2-haloalkoxy, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
R6 is hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra, RaO, RaS(O)m, RaOxe2x80x94(Cxe2x95x90O), Ra(Cxe2x95x90O), RaRbNxe2x80x94(Cxe2x95x90O), RaHNxe2x80x94(Cxe2x95x90O), H2Nxe2x80x94(Cxe2x95x90O), Raxe2x80x94(Cxe2x95x90O)xe2x80x94NH, Raxe2x80x94(Cxe2x95x90O)xe2x80x94NRb or RaOxe2x80x94Nxe2x95x90C(Rb);
Ra, Rb are C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, each of which may be substituted by cyano, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl, or are phenyl which may carry one to three substituents selected from the group consisting of halogen and C1-C4-alkyl, and
the radicals R1 to R3 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group If in which
R1, R3 are cyano, C1-C8-alkyl, propynyl, C1-C2-haloalkyl or cyclopropyl and are preferably methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R2 is halogen or C1-C8-alkyl and is preferably fluorine, chlorine, methyl or ethyl;
R4, R8 are hydrogen;
R5, R7 independently of one another are hydrogen, cyano, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, cyano, Ra or RaOxe2x80x94Nxe2x95x90C(Rb);
R6 is hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and is preferably hydrogen, halogen or C1-C4-alkyl and
Ra, Rb are C1-C4-alkyl.
Group Ig: 2-(N-phenylamino)pyrimidines of the formula I in which
R1 is cyclopropyl;
R3 is cyano, C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals alkyl, alkenyl and alkynyl may be substituted by cyano, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, or is C3-C8-cycloalkyl;
the radicals R2 and R4 to R8 are each as defined in claim 1.
Preference is given to 2-(N-phenylamino)pyrimidines of the group Ig in which
R1 is cyclopropyl;
R2 is halogen or C1-C8-alkyl and is preferably fluorine, chlorine, methyl or ethyl;
R3 is cyano, C1-C8-alkyl, propynyl or cyclopropyl and is preferably methyl, ethyl, n-propyl, propynyl or cyclopropyl;
R4 to R8 independently of one another are hydrogen, cyano, halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, Ra or RaOxe2x80x94Nxe2x95x90C(Rb) and are preferably hydrogen, halogen or C1-C4-alkyl and
Ra, Rb are C1-C4-alkyl.
Examples of particularly preferred 2-(N-phenylamino)pyrimidines are compiled in the Tables below.
2-(N-phenylamino)pyrimidines I.1-001 to I.1-379 of the formula I.1.
2-(N-phenylamino)pyrimidines I.2-001 to I.2-379 of the formula I.2, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.3-001 to I.3-379 of the formula I.3, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.4-001 to I.4-379 of the formula I.4, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.5-001 to I.5-379 of the formula I.5, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.6-001 to I.6-379 of the formula I.6, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.7-001 to I.7-379 of the formula I.7, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.8-001 to I.8-379 of the formula I.8, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.9-001 to I.9-379 of the formula I.9, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.10-001 to I.10-379 of the formula I.10, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.11-001 to I.11-379 of the formula I.11, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.12-001 to I.12-379 of the formula I.12, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.13-001 to I.13-379 of the formula I.13, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.14-001 to I.14-379 of the formula I.14, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.15-001 to I.15-379 of the formula I.15, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.16-001 to I.16-379 of the formula I.16, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.17-001 to I.17-379 of the formula I.17, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.18-001 to I.18-379 of the formula I.18, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.19-001 to I.19-379 of the formula I.19, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.20-001 to I.20-379 of the formula I.20, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.21-001 to I.21-379 of the formula I.21, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.22-001 to I.22-379 of the formula I.22, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.23-001 to I.23-379 of the formula I.23, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.24-001 to I.24-379 of the formula I.24, in which the meaning of (Rx)p is given by the rows of Table 1.
2-(N-phenylamino)pyrimidines I.25-001 to I.25-379 of the formula I.25, in which the meaning of (Rx)p is given by the rows of Table 1.
The compounds I are suitable for use as fungicides. They have outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically, and they can be employed in crop protection as foliar- and soil-acting fungicides.
They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugar cane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.
Specifically, they are suitable for controlling the following plant diseases:
Alternaria species on vegetables and fruit,
Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines,
Cercospora arachidicola on peanuts,
Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,
Erysiphe graminis (powdery mildew) on cereals,
Fusarium and Verticillium species on various plants,
Helminthosporium species on cereals,
Mycosphaerella species on bananas and peanuts,
Phytophthora infestans on potatoes and tomatoes,
Plasmopara viticola on grapevines,
Podosphaera leucotricha on apples,
Pseudocercosporella herpotrichoides on wheat and barley,
Pseudoperonospora species on hops and cucumbers,
Puccinia species on cereals,
Pyricularia oryzae on rice,
Rhizoctonia species on cotton, rice and turf,
Septoria nodorum on wheat,
Uncinula necator on grapevines,
Ustilago species on cereals and sugar cane, and
Venturia species (scab) on apples and pears.
Moreover, the compounds I are suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, paint dispersions, fibers and fabrics) and in the protection of stored products.
The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application can be effected both before and after infection of the materials, plants or seeds by the fungi.
In general, the fungicidal compositions comprise from 0.1 to 95, preferably 0.5 to 90, % by weight of active ingredient.
When used in crop protection, the rates of application are from 0.01 to 2.0 kg of active ingredient per ha, depending on the nature of the desired effect.
In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.
When used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and on the desired effect. Rates of application conventionally used in the protection of materials are, for example, from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.
The compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.
The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The following are examples of formulations:
I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.
II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a formulation of the active ingredient with good adhesion properties (comprises 23% by weight of active ingredient).
III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).
IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).
V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).
VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-xcex1-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).
VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-xcex1-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.
The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active ingredients according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.
The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.
Various types of oils, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.
In the use form as fungicides, the compositions according to the invention can also be present together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides frequently results in a broader fungicidal spectrum of action.
The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:
sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,Nxe2x80x2-propylenebisdithiocarbamate), zinc (N,Nxe2x80x2-propylenebisdithiocarbamate), N,Nxe2x80x2-polypropylenebis(thiocarbamoyl)disulfide;
nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitro-isophthalate;
heterocyclic substances, such as 2-heptadecyl-2-imidazoline 45 acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]-quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;
N-dichlorofluoromethylthio-Nxe2x80x2,Nxe2x80x2-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol 1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, cyclohexyl 2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-Nxe2x80x2-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS, 3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, xcex1-(2-chlorophenyl)-xcex1-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene;
strobilurins such as methyl E-methoxyimino-[xcex1-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate, methyl-E-methoxyimino-[xcex1-(2-phenoxyphenyl)]acetamide, methyl-E-methoxyimino-[xcex1-(2,5-dimethylphenoxy)-o-tolyl]acetamide;
anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline;
phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile;
cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine;
and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2xe2x80x2-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-xcex1-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoro-methyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.